Yes, Billy Bowlegs is an actual historical figure named William Augustus Bowles. It is believed that the nickname was not because he had bowed legs, but just an evolution of his last name of Bowles. He is best known as a pirate and adventurer who lobbied for the rights of Native Americans in the late 1700s.
Born in Maryland in 1763, Bowles was a loyalist. He joined the British Army at the age of 13 and fought on behalf of the King in the American Revolution. He soon found his way into the British Navy, which brought him to the port of Pensacola. While in Pensacola, Bowles was dismissed from the Navy for dereliction of duty. Stranded and jobless, he went about making a life for himself on the Gulf Coast.
Bowles joined the Creek Indians who frequented the area, and for two years he assimilated to the Indian way of life. He lived nomadically while hunting and fishing along Pensacola Bay. For a short time, he worked for a baker in Pensacola.
In 1781, as the Spanish prepared to attack British-ruled Pensacola, Bowles organized the Chattahoochee Creeks to fight on behalf of the British. Dressed in a Creek hunting jacket, Bowles led an Indian war party against the Spanish in the Siege of Pensacola. He was only 17 at the time. When the battle was lost, Bowles and the Creeks escaped back into the woods.
After the Revolutionary War, Bowles pursued support for his idea of an American Indian state. Representing the Creek and Cherokee nations, he was received by George III of England. With British support, he sailed back to Florida. In 1795, along with the Seminoles, he formed a short-lived state in northwest Florida known as Muskogee. Bowles named himself president, and in 1800 he declared war on Spain. The Muskogee forces consisted of two schooners and 400 frontiersmen, freed slaves and Indian warriors.
A furious Spain offered a bounty of $6,000 and 1,500 bottles of rum for Bowles. He was eventually captured and taken to Madrid. The King of Spain encouraged him to switch sides and sway Indian favor to the Spanish. Instead, Bowles escaped imprisonment and commandeered a ship. He sailed to Africa and then made his way back to the Gulf of Mexico.
In 1803, not long after he declared himself Chief of all Indians Present, Bowles was betrayed and recaptured by the Spanish. He died in prison in Havana two years later after having refused to eat.
Although William Bowles is affectionately called Billy Bowlegs, his legend also lives on in his Indian name, Estajoca.
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